3,5-Dibromopyridine → HCID 18187614, compound

Participants

Role	Name	HCID	Charge
Reactant	3,5-Dibromopyridine	HCID 69369	—
Reactant	HCID 178419663	HCID 178419663	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Catalyst	Zincchloride	HCID 3007855	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Tetrahydrofuran	HCID 8028	—
Product	HCID 18187614	HCID 18187614	—

Reaction Conditions

Temperature	50 °C

Reaction Steps

Benzylmagnesium bromide (1.0 M in THF, 20 mL, 20 mmol) was added to a solution of zinc chloride (2.73 g, 20 mmol) in THF (20 mL) and the reaction was heated to 50° C. for 2.5 hours. The solution was then added by cannula to a solution of 3,5-dibromo-pyridine (3.07 g, 13 mmol), copper(I) iodide (0.0148 g, 0.78 mmol), and (1,1′-bis(diphenylphosphino)ferrocene)-dichloropalladium(II) (0.048 g, 0.65 mmol) in THF (20 mL). The reaction was heated to 50° C. for 48 hours then quenched with H2O, submitted to standard aqueous workup, and purified via silica gel chromatography (0-50% EtOAc in hexanes) to give the title compound.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08778983B2
Source dataset	uspto-grants-2014_07
ORD ID	ord-38b105fd3cb343f4b857adc0ea1cd853
Source note	uspto-grants-2014_07